Water → Tert-butyl 4-cyano-4-(2-hydroxyethyl)piperidine-1-carboxylate

HRID 412584Notes

Reaction equation

HRID 412584 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:19]#[N:20])([CH2:14][CH:15]([OH:18])CO)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+].O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:19]#[N:20])([CH2:14][CH2:15][OH:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 600641754-Cyano-4-(2,3-dihydroxypropyl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 60064207Tert-butyl 4-cyano-4-(2-hydroxyethyl)piperidine-1-carboxylateYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-cyano-4-(2,3-dihydroxypropyl)piperidine-1-carboxylic acid tert-butyl ester (3.65 g) in tetrahydrofuran (100 ml) was added 10% aqueous sodium periodate solution (100 ml), and the mixture was stirred at room temperature for 40 min. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained residue (3.3 g) was dissolved in tetrahydrofuran (100 ml) and sodium borohydride (360 mg) and methanol (20 ml) were added with ice-cooling, and the mixture was stirred at room temperature for 30 min. After completion of the reaction, 10% aqueous citric acid was added and the mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=95:5) and dried under reduced pressure to give the title compound (3.13 g).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. dissolutionThe obtained residue (3.3 g) was dissolved in tetrahydrofuran (100 ml)
  7. additionsodium borohydride (360 mg) and methanol (20 ml) were added with ice-
  8. temperaturecooling
  9. stirringthe mixture was stirred at room temperature for 30 min
  10. customAfter completion of the reaction, 10% aqueous citric acid
  11. additionwas added
  12. extractionthe mixture was extracted with ethyl acetate
  13. washwashed with saturated brine
  14. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  15. customthe solvent was evaporated
  16. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=95:5)
  17. customdried under reduced pressure

Sources & evidence

ORD record
ord-76f457d9a39741b0bf617669a7e6329d
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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